CA2426103A1 - New cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including thus resistant to usual chemotherapeutic agents and as reversal agents - Google Patents

New cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including thus resistant to usual chemotherapeutic agents and as reversal agents Download PDF

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Publication number
CA2426103A1
CA2426103A1 CA002426103A CA2426103A CA2426103A1 CA 2426103 A1 CA2426103 A1 CA 2426103A1 CA 002426103 A CA002426103 A CA 002426103A CA 2426103 A CA2426103 A CA 2426103A CA 2426103 A1 CA2426103 A1 CA 2426103A1
Authority
CA
Canada
Prior art keywords
dichloromethane
mmol
alkyl
ome
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002426103A
Other languages
English (en)
French (fr)
Inventor
Jean-Pierre Robin
Robert Dhal
Freddy Drouye
Jean-Pierre Marie
Nina Radosevic
Julie Robin
Karine Souchaud
Patricia Bataille
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ChemGenex Pharmaceuticals Pty Ltd
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2426103A1 publication Critical patent/CA2426103A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/20—Spiro-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/20—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/20—Spiro-condensed systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Oncology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Hematology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA002426103A 2000-10-17 2000-10-17 New cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including thus resistant to usual chemotherapeutic agents and as reversal agents Abandoned CA2426103A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2000/001593 WO2002032904A1 (en) 2000-10-17 2000-10-17 New cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including thus resistant to usual chemotherapeutic agents and as reversal agents

Publications (1)

Publication Number Publication Date
CA2426103A1 true CA2426103A1 (en) 2002-04-25

Family

ID=11003995

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002426103A Abandoned CA2426103A1 (en) 2000-10-17 2000-10-17 New cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including thus resistant to usual chemotherapeutic agents and as reversal agents

Country Status (12)

Country Link
US (1) US6579869B1 (enExample)
EP (1) EP1328527B1 (enExample)
JP (1) JP4837233B2 (enExample)
CN (1) CN1303084C (enExample)
AT (1) ATE319714T1 (enExample)
AU (1) AU7940500A (enExample)
CA (1) CA2426103A1 (enExample)
DE (1) DE60026557T2 (enExample)
DK (1) DK1328527T3 (enExample)
ES (1) ES2258024T3 (enExample)
PT (1) PT1328527E (enExample)
WO (1) WO2002032904A1 (enExample)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7285546B2 (en) * 2000-10-17 2007-10-23 Stragen Pharma S.A. Cephalotaxanes, their method of preparation and their use in treatment of cancers, leukemias, parasites including those resistant to usual chemotherapeutic agents and as reversal agents
US20020128258A1 (en) * 2001-03-09 2002-09-12 Jean-Pierre Robin Therapeutical method involving subcutaneous administration of drugs containing cephalotaxine derivatives
WO2004009092A1 (en) * 2002-07-17 2004-01-29 Chemgenex Pharmaceuticals Limited Formulations and methods of administration of cephalotaxines, including homoharringtonine
US7642252B2 (en) 2002-07-22 2010-01-05 Chemgenex Pharmaceuticals, Inc. Angiogenesis inhibition by cephalotaxine alkaloids, derivatives, compositions and uses thereof
WO2009148654A2 (en) 2008-03-03 2009-12-10 Sloan-Kettering Institute For Cancer Research Cephalotaxus esters, methods of synthesis, and uses thereof
US20120022250A1 (en) * 2009-03-11 2012-01-26 Jean-Pierre Robin Process for preparing cephalotaxine esters
CN102304132B (zh) * 2011-07-12 2015-01-28 南开大学 高效高立体选择性半合成三尖杉酯类生物碱的方法
CN103687859B (zh) * 2011-08-18 2016-08-17 杭州本生药业有限公司 高三尖杉酯碱的胺化衍生物、及其制备方法和应用
CN102675327B (zh) * 2012-03-01 2014-12-10 南开大学 三尖杉酯碱类似物及制备方法和应用
CN104293855A (zh) * 2014-10-15 2015-01-21 中国计量学院 脐孢木霉菌转化株在提高木霉素产量中的应用
US10597401B2 (en) 2015-05-08 2020-03-24 Albany Molecular Research, Inc. Methods and intermediates for the preparation of omacetaxine and cephalotaxine derivatives thereof
CN106866690B (zh) * 2015-12-10 2019-10-11 南开大学 三尖杉酯类生物碱、其制备方法和用途
CN109111459B (zh) * 2017-06-22 2021-10-29 南华大学 含水杨酸三尖杉碱酯衍生物、制造方法及其用途
CN108378049A (zh) * 2018-05-02 2018-08-10 孙利嫚 一种含有粗榧生物碱和甲氧虫酰肼的农药组合物
TW202421631A (zh) * 2022-09-22 2024-06-01 南開大學 三尖杉酯鹼類衍生物及其藥物組合物、製備方法和用途
KR20250160078A (ko) * 2024-05-03 2025-11-11 주식회사 아론티어 암 연관 섬유아세포 표적용 약학 조성물

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2776292B1 (fr) * 1998-03-20 2004-09-10 Oncopharm Cephalotaxanes porteurs de chaine laterale et leur procede de synthese

Also Published As

Publication number Publication date
ES2258024T3 (es) 2006-08-16
EP1328527B1 (en) 2006-03-08
WO2002032904A1 (en) 2002-04-25
AU7940500A (en) 2002-04-29
DE60026557T2 (de) 2006-12-28
JP2004511560A (ja) 2004-04-15
US6579869B1 (en) 2003-06-17
PT1328527E (pt) 2006-06-30
CN1474821A (zh) 2004-02-11
ATE319714T1 (de) 2006-03-15
DE60026557D1 (de) 2006-05-04
EP1328527A1 (en) 2003-07-23
HK1063183A1 (en) 2004-12-17
CN1303084C (zh) 2007-03-07
JP4837233B2 (ja) 2011-12-14
DK1328527T3 (da) 2006-07-17

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EEER Examination request
FZDE Discontinued

Effective date: 20130404